P-Anisidine → 7-(2-Methoxyphenyl)-3-(4-methoxyphenyl)thieno[3,2-d]pyrimidin-4(3H)-one

HRID 1775657Notes

Reaction equation

HRID 1775657 reaction equation
[C:1]1([N:7]2[C:12](=[O:13])[C:11]3[S:14][CH:15]=[C:16]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[C:10]=3[N:9]=[CH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.NC1C(C2C=CC=C[C:30]=2[O:35]C)=CSC=1C(OC)=O.[CH:41](OCC)(OCC)[O:42]CC.COC1C=CC(N)=CC=1>C(O)(=O)C>[CH3:30][O:35][C:22]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:16]1[C:10]2[N:9]=[CH:8][N:7]([C:1]3[CH:6]=[CH:5][C:4]([O:42][CH3:41])=[CH:3][CH:2]=3)[C:12](=[O:13])[C:11]=2[S:14][CH:15]=1

Participants

6

Reactant 4

HCID 7732P-AnisidineHCID 31214Ethyl orthoformateHCID 11311579HCID 11311579, compoundHCID 783248653,7-Diphenylthieno[3,2-d]pyrimidin-4(3H)-one

Product 1

HCID 783220637-(2-Methoxyphenyl)-3-(4-methoxyphenyl)thieno[3,2-d]pyrimidin-4(3H)-oneYield 56.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In the same manner as the synthesis of Compound 1, methyl 3-amino-4-(2-methoxyphenyl)thiophene-2-carboxylate (40 mg, 0.15 mmol), triethyl orthoformate (0.33 ml), p-anisidine (34.8 mg, 0.28 mmol), and acetic acid (0.04 ml) were used to give 31 mg (0.09 mmol, 56.7% yield) of the title compound.

Sources & evidence

ORD record
ord-e8919dec143e47f2858dd6a1123b90e9
Source dataset
uspto-grants-2016_02
Patent number
US09260448B2

Reaction notes

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